So You Want to Quit Your Job and “Start Over”?

In the fall of 2008, soon after the global financial crisis took hold, I quit my full-time job, returned part-time to teaching, and started editing and writing on a freelance basis. The decision was the right one for me for a variety of reasons, and I’m very happy to be back in the classroom. But the move wasn’t the wildly liberating rebirth that people often assume a voluntary career transition to be. It simply marked a new phase in a continuous personal evolution. No fireworks went off. No balloons soared. I didn’t speak in tongues.

That humdrum reality is at odds with a template in the American psyche about the nature of self-renewal. Its features include casting off the shackles of the past, reinventing yourself, and realizing a full potential that only “starting over” supposedly permits. The deceptive allure of Jay Gatsby’s “orgastic future” is alive and well 85 years after F. Scott Fitzgerald’s novel was published.

The American corporate workplace is the perfect breeding ground for this fantasy, with its almost pathological preoccupation with invention and innovation as metaphors for progress. Don’t get me wrong, these concepts are extremely useful when it comes to developing products and services, as the history of business proves in spades. But their psychological reach extends far beyond the domains where they have practical value. Indeed, the conceptual power of invention and innovation has been swallowed whole by many people who, naturally, feel the itch to change their lives from time to time, whether professionally or personally.

It’s just plain misguided to view that itch as evidence of a fundamental product flaw that requires you, as self-engineer, to go back to the drawing board and come up with a new design. Nor is it a malady in need of a cure or an evil from which to seek deliverance. The itch simply comes with having skin and flesh and blood and bone. As you walk through the world and its underbrush, you’re bound to get thorns in your side. No need to undergo a major surgical procedure to extract them — or to self-righteously cast blame elsewhere for being pricked. Save the stinging resignation sermon for the pulpit in your head.

Yes, I feel a bit uncomfortable when I listen to folks evangelize about reinventing themselves by quitting a job — or when they ask me to evangelize about my own quitting experience. It’s not that I get offended (I rarely do about anything), but I can’t help but be disturbed when I witness people playing tricks on their own minds, perhaps because I have done it myself. As I’ve written before, hyperbole about new-found freedom gets old fast, setting you up for a big letdown or even a crash and burn.

But perhaps this, too, sounds like evangelizing — by someone who’s written one too many blog posts about quitting a job. Call me a hypocrite. I won’t be offended.

About Steven DeMaio
Steven DeMaio teaches English and math at the Community Learning Center in Cambridge, Massachusetts, and the Somerville Center for Adult Learning Experiences in Somerville, Massachusetts. He also works as a freelance editor and writer. This is a continuation of his blog that ran for 10 months in 2009 on

7 Responses to So You Want to Quit Your Job and “Start Over”?

  1. Will says:

    Hi Steven,

    I just discovered your blog posts on and read nearly all of them. Now I’m reading your new blog. Please keep it up, it’s wonderfully written and hits the mark perfectly.

    I’m a journalist who’s been lucky enough to have enjoyed great success in the short time I’ve been in the field. I was an editor at an online magazine at 26, promoted to editor-in-chief at 28, and left that job to become an editor at a much larger online magazine at 29. Now I’m 31 and I find myself deeply unsatisfied with this job that I worked so many years to ascend to. It’s left me feeling like I don’t know who I am anymore.

    I took the quiz on your previous blog — the one that helps you figure out whether you’re feeling fulfilled by your work — and scored mostly C’s. It made me realize why I’m unhappy where I’m currently employed. This job gives me plenty of money (a ridiculous amount, in my opinion) and influence (my work is read by hundreds of thousands of people each week) and I love my coworkers (the sole “A” that I scored on the quiz was to the question of whether I laugh a lot at work.)

    The problem is that the work doesn’t matter. It’s fun, sure, but it’s fleeting, inconsequential, and I’ll never meet most of the people who read it. It suddenly seems quite depressing.

    I’m considering quitting the job this June after just a year and a half of working there. It doesn’t feel like things are going to turn around — if anything, the downward slide feels like it’s accelerating. Quitting feels like throwing away the very thing I’ve worked so hard for years to attain, and maybe the most foolish thing I could ever do. Not to mention how naive and whimsical I worry I’ll appear to my friends, family, and coworkers.

    We’ll see what the next few months bring.

    • Ricardo says:

      Hey Will,

      I really felt the need to reply to you comment. I have currently worked for the company I am with for over 6 years. I have hung in there thru really rough times for the company. I always had the mind set that I didn’t want to throw it all away. The company has always promised some things but to this date none of it has happened. Now, the company has been taken over by a new board and things have gotten even worse. I now feel like I have really wasted all this time in staying because I have been unhappy for a really long time. There used to be a time when I loved coming to work but those days are only a memory now. The bottom line here is that you have to be happy…You have to do the things that you happy. You really are not throwing anything away because you also invested all of that time in yourself with all the things you learned. For me its been a really hard lesson because I stayed because I loved the product I supported, the people I worked with and even the customers. I still stayed after the company lowered salaries, took away all of our perks such as the ability to work from home.

      Good luck!

  2. Will,

    First, I’m flattered that you read so many of my posts. The quiz you mention had fallen even off my own radar, but you made me look at it (and enjoy it) again.

    It sounds as though you’re doing precisely the kind of nuanced reflection that will lead you to the best decision for you. That doesn’t mean it isn’t a tough haul, as your comment makes clear. But the fact that you can capture what you’re going through in words so well is about as good a sign as there is.

    I wish you the best and hope to hear from you again.

    Steve DeMaio

  3. I’m really glad you wrote this Steve. Thank you for articulating it.

    The best way to be successful on your own is to keep things simple. Especially at first. And the best place to start practicing this is with your own expectations. Plan some things out, but keep it simple and be surprised when you exceed it.

  4. Bob says:

    Am I in a good financial position to quit my job? I got 75k in cash, no debt, no dependents, tenants paying for my mortgages, totally bored with my job, and the $100k salary doesnt matter as much anymore. I thnk I can cut monthly expenses down to 2k a month I want to take some time to travel, write, study, etc.

  5. Sam says:

    I enjoyed your HBR blog post and this follow-up one. I quit my job the first of the month. I am 29, young and brash, without a family. I have some savings; nothing like the previous poster Bob has.

    I am not looking for freedom, just a chance of pace. Hopefully I can find something that respects me and my ideas. I may not be always right, but at least treat me like I’m right.

    It is a difficult road out there, but I know with persistence I can get something better.

  6. Pavithra says:

    I stumbled upon your HBR blog “I quit my job. Am I crazy?” a few days after I resigned a comfortable, well-paying job in an IT company, to be “self-indulgent” and teach, study and write. I found it immensely comforting reading through your posts – while encouraging, the experience has also been a reality check. Initially, I was quite sure this move would make space for me to find my “great work”, but in the face of skepticism from family and friends, I’m petrified. But I’m not withdrawing that resignation yet…

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